Small talk doesn’t have to be tedious for those who are curious how people make a living in the Bay Area. There seem to be endless ways to make money here—and if someone asks someone what they do for a living, they often receive more than one answer.
What does that reality do to a person’s life and trajectory? If we need multiple sources of income to survive but can’t commit to one path long enough to advance, are we moving forward—or just staying afloat?
I’m also challenging my own biases. As a freelance writer, my financially necessary day job often keeps me from pouring myself into the creative work I find most fulfilling.
For some, security means a regulated schedule, consistent salary and benefits. For others, multiple income streams offer a greater sense of stability, according to labor researcher Jane Collins, PhD.
“There was a lot of talk about feeling overwhelmed and like you couldn’t give your full attention to each job,” Collins said. “But then other people were saying, ‘I don’t want to be doing 9-to-5 work.’ They like combining different things, using different skills. Or they could lose that main job at any time, so they have to have something to fall back on.”
In her 2024 paper, The Semi-Proletarian Lifestyle in the Twenty-First Century, Collins examines the historical context of multiple jobholding and what she describes as “having to do a lot of different things to survive.”
Wage stagnation is a major factor. “Since at least 1980 … wages have stayed flat in a way that historically we haven’t seen before,” Collins said. “They’ve risen, but they haven’t risen much more than the rate of inflation.”
Employers often offset labor costs by cutting hours and by hiring significantly more part-time workers or non-employed contracted workers, who they aren’t required to pay employment taxes on. This reduces the cost of benefits, as large companies with over 50 employees are required to offer health coverage to employees working 30-plus hours a week, per the Affordable Care Act.
After the 2021 “Great Resignation,” the balance of power briefly shifted toward workers—but in 2026, the job market feels far less certain.
“That job posting you applied to three weeks ago? It was never real,” wrote Erik Chavez, 40, a senior solutions engineer at Microsoft and founder of the AI startup Jobric. A recruiter told him a role had been listed for eight months “with no intention to fill it.”
“Let’s be honest, searching for a job is exhausting,” Chavez said. “You’re scrolling endless job boards, sifting through LinkedIn posts, fielding recruiter messages, reaching out to everyone you know, hoping for a lead… . Nearly every tool in this space was built for employers and recruiters, not candidates.”
Chavez built Jobric on the side to address that imbalance. For him, multiple streams of work aren’t about survival but about ambition. Being the head engineer of his own project along with a full-time job keeps Chavez’s schedule tight, but dedication to problem-solving keeps him focused.
“Start small, stay consistent and increase the intensity as you build momentum,” he said. “Between a demanding full-time role and the hours I’m putting into Jobric, it would be easy to let self-care slip. But that’s a trap.”
Work-life balance can be an afterthought, especially for entrepreneurs, freelancers and business owners. These individuals may have diverging lifestyles and challenges, but a strong work ethic is the link they share.
Leilani Lawson offers a different perspective. A bartender, Lyft driver, in-home caretaker, hairstylist, student and single mother, she pieces together income across the East Bay.
“I don’t have a social life really right now—that’s nonexistent,” Lawson said. “So that’s what I love about bartending; I love to network and socialize.”
Raised in foster care, Lawson learned early how to survive. “Before you even turn 18 it’s, ‘How am I going to get my next meal? Where am I going to sleep tonight?’ You learn how to hustle.”
In adulthood, that survival instinct became entrepreneurship. She studies cosmetology, braids hair and approaches potential clients directly: “I’ll literally [ask], ‘Who braids your hair?’” she said.
Lawson is an example of someone who speaks her ambition into reality by unapologetically asserting herself. Though her schedule is hectic, she values the freedom that comes with having various sources of income.
“Doing multiple things, I’m able to change my environment,” she said. “I hate feeling stagnant and stuck, so being able to switch up my roles and switch up my jobs gives me that freedom. Living in the Bay Area, you can pick up a hustle at the drop of a dime.”
During her 10-year career as a bartender, Lawson developed sharp skills and built great success in that industry. However, she began to expand her income sources for more stability.
After losing a lucrative bartending job when The Moxie closed, Lawson expanded into in-home care for greater stability. The role now provides benefits and a sense of purpose.
“I really do like to look after people and help people,” she said.
Talking with Lawson and Chavez reshaped how I think about work. What I once saw as a burden can, in some cases, be reframed as flexibility—or even opportunity. Not because we should commit to grating work for the sake of conventional success; but because opportunities are vast when we assert ourselves. I’m only doing too much if I’m doing the wrong thing.
But that reframing comes with a cost. For some, multiple jobs are a path to growth. For others, they’re the only way to stay afloat.
In the Bay Area, doing “too much” may simply be what it takes to get by—or to get ahead.
